2,2,2-Trifluoroethanol → HCID 67251456, compound

HRID 2427742Notes

Reaction equation

HRID 2427742 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[C:7](=[O:12])[N:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[CH2:5]2.C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+].[F:56][C:57]([F:61])([F:60])[CH2:58][OH:59]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:56][C:57]([F:61])([F:60])[CH2:58][O:59][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[C:7](=[O:12])[N:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[CH2:5]2

Participants

7

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 10796Cesium carbonateHCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphineHCID 116393035-Bromo-7-chloro-2-(4-chloro-benzyl)-2,3-dihydro-isoindol-1-one

Product 1

HCID 67251456HCID 67251456, compoundYield 34.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-bromo-7-chloro-2-(4-chloro-benzyl)-2,3-dihydro-isoindol-1-one (0.110 g, 0.298 mmol), palladium(II) acetate (0.004 g, 0.02 mmol), rac-2-(di-t-butylphosphino)-1,1′-binaphthyl (0.009 g, 0.025 mmol), and cesium carbonate (0.163 g, 0.5 mmol) in toluene (5 mL) was treated with 2,2,2-trifluoro ethanol (0.061 mL, 0.6 mmol) and stirred at 110° C. for 12 h. After this time the solvent was evaporated and silica gel column chromatography using, typically 30% ethyl acetate in hexane, afforded the desired product (0.040 g, 34%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.19 (s, 2H), 4.39 (q, 2H), 4.73 (s, 2H), 6.86 (s, 1H), 6.98 (s, 1H), 7.23 (d, 2H), 7.34 (d, 2H). GC-MS: m/z 389 (M)+0.354, (M−35)+.

Workup

  1. customAfter this time the solvent was evaporated

Sources & evidence

ORD record
ord-5036f36fbdd944b0ae9070de1a98454e
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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